通过亨利反应短程高效合成(2S,3R,4R,5R)和(2S,3R,4R,5S)-四羟基氮杂环庚烷
Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction.
作者信息
Chakraborty Chaitali, Dhavale Dilip D
机构信息
Garware Research Centre, Department of Chemistry, University of Pune, Pune 411 007, India.
出版信息
Carbohydr Res. 2006 May 22;341(7):912-7. doi: 10.1016/j.carres.2006.02.007. Epub 2006 Mar 3.
The Henry reaction with the easily available alpha-d-xylo-pentodialdose afforded a diastereomeric mixture of nitroaldoses with the alpha-d-gluco- and beta-l-ido-configuration, respectively, in good yield. When n-BuLi was used as the base, the reaction afforded the alpha-d-gluco-nitroaldose as the only product. The reduction of the nitro group in the alpha-d-gluco- and beta-l-ido-nitroaldoses, removal of the protecting groups and intramolecular reductive cyclo-amination afforded the corresponding (2S,3R,4R,5R) and (2S,3R,4R,5S) tetrahydroxyazepanes.
亨利反应中，使用易于获得的α-D-木糖戊二醛糖，分别以良好的产率得到了具有α-D-葡萄糖和β-L-艾杜糖构型的非对映体硝基醛糖混合物。当使用正丁基锂作为碱时，反应仅得到α-D-葡萄糖硝基醛糖作为唯一产物。α-D-葡萄糖硝基醛糖和β-L-艾杜糖硝基醛糖中硝基的还原、保护基团的去除以及分子内还原环胺化反应得到了相应的(2S,3R,4R,5R)和(2S,3R,4R,5S)四羟基氮杂环庚烷。
Zotero 插件